Tommy Paul vs. Flavio Cobolli Prediction, Pick for Cincinnati Open – 8/20/26

American Tommy Paul faces Flavio Cobolli at the Cincinnati Open on Thursday afternoon in a compelling men’s quarterfinal matchup.

Paul is fresh off an upset of world No. 3 Alexander Zverev, while Cobolli continues to enjoy a banner campaign that includes a runner-up finish at the 2026 French Open.

Below, we’ll break down our Tommy Paul vs. Flavio Cobolli prediction, including recent form, match analysis, and a PrizePicks pick. The match is slated to start at 3 p.m. ET on Tennis Channel.

Make your Cincinnati Open predictions on PrizePicks for Thursday’s match now!

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Tommy Paul vs. Flavio Cobolli Prediction, Favorite for the Cincinnati Open Quarterfinals

Below are the payouts for who will win Thursday’s Paul vs. Cobolli match, via PrizePicks Team Picks. 

On PrizePicks Team Picks, a 2x payout represents a return of $200 on a $100 entry (or $20 on $10). A lower payout multiplier signals a higher implied probability of that result based on user picks.

Payouts are live at the time of writing and are subject to change. Tennis winner markets are available in 36 states.

Tommy Paul vs. Flavio Cobolli Cincinnati Open Prediction – Thursday, August 20

Match Winner Payouts: Paul 1.58x | Cobolli 2.27x
Tournament Round: Quarterfinals
2026 Record Entering the Cincinnati Open: Paul 33-15 | Cobolli 27-17
Head-to-Head Record: Cobolli leads 1-0
Scheduled Time: 3:00 p.m. ET
How to Watch: Tennis Channel

Following underwhelming results in both Washington and Montreal, few probably expected Tommy Paul to best top seed Alexander Zverev in the last round.

And yet, Paul did in fact do just that, winning a tight 4-6, 7-6(6), 6-4 three-setter over the 2026 French Open champion.

Including his three Cincinnati victories, Paul is now up to 36 wins on the season, putting him among the ATP Tour leaders. That includes a solid 18-9 record on hard courts, a surface where he owns a 60.8% career win rate.

Flavio Cobolli also arrived at this event in questionable form after first-round exits at both Umag and Montreal. While it hasn’t been a smooth ride to these quarterfinals after enduring three straight three-setters, he earned a big win over rising star Rafael Jodar in the last round.

The 24-year-old Italian is in the midst of a career year, cracking the top 10 for the first time following a runner-up finish at this year’s French Open. 

However, hard courts have historically been his weakest surface. While Cobolli won a hard-court title in Acapulco this year, he’s also been one-and-done at the Australian Open, Montpellier, Dallas, Miami, and most recently Montreal. In fact, he entered this tournament with a .500 career record on the surface. 

According to Tennis Abstract’s Elo ratings, Paul is the superior player on hard courts and projects to win 59.1% of the time. He’ll also enjoy home-court advantage playing in front of an American crowd. 

Make your Paul vs. Cobolli Cincinnati Open prediction on PrizePicks now!

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Tommy Paul vs. Flavio Cobolli Pick for the Cincinnati Open on Thursday

Both players have gone to a deciding third set in every match they’ve played here. Paul’s matches have totaled 32, 28, and 33 games while Cobolli’s have reached 26, 34, and 32 games.

Although Cobolli is the underdog in this match, he won their only previous encounter at the 2024 Cincinnati Open. He won 6-2, 4-6, 7-5 across 30 total games.  

The Italian has played six hard-court matches against top-50 opponents this year and five have gone to a third set and/or included a tiebreak set.

Cobolli is tied for the fifth-most tiebreaks (29) played this season among the top 50 players. That includes 14 on hard courts across just 17 matches.

Paul vs. Cobolli Pick – 23.5 Total Games

Make Your Cincinnati Open Predictions Today on PrizePicks

Both Tommy Paul and Flavio Cobolli enter this match with renewed confidence following their big wins in the previous round. Which player will come out on top and book a spot in the semifinals?

Don’t wait until Thursday’s matches start — make your Cincinnati Open predictions on PrizePicks now.

Pick your players, predict More or Less on their stats like games won or aces, or make match winner predictions with Team Picks, available in 36 states!

Stay locked in on Playbook for daily tennis predictions, tennis picks, and PrizePicks analysis throughout the tournament.